JP4825992B2 - Acrylic pressure-sensitive adhesive composition, method for producing pressure-sensitive adhesive tape using the composition, and pressure-sensitive adhesive tape - Google Patents

Acrylic pressure-sensitive adhesive composition, method for producing pressure-sensitive adhesive tape using the composition, and pressure-sensitive adhesive tape Download PDF

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JP4825992B2
JP4825992B2 JP22757999A JP22757999A JP4825992B2 JP 4825992 B2 JP4825992 B2 JP 4825992B2 JP 22757999 A JP22757999 A JP 22757999A JP 22757999 A JP22757999 A JP 22757999A JP 4825992 B2 JP4825992 B2 JP 4825992B2
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meth
acrylic acid
weight
sensitive adhesive
pressure
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JP2001049200A (en
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沢 光 彦 中
沢 容 一 滝
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綜研化学株式会社
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Description

[0001]
TECHNICAL FIELD OF THE INVENTION
The present invention relates to an acrylic pressure-sensitive adhesive composition substantially free of a solvent, a pressure-sensitive adhesive tape using the composition, and a method for producing the pressure-sensitive adhesive tape.
[0002]
[Prior art]
Conventionally, rubber-based adhesives and synthetic rubbers have been used as pressure-sensitive adhesives, but sufficient adhesive strength cannot be obtained with these components alone. In order to impart effective properties to such pressure-sensitive adhesives, tackifiers such as rosin acid derivatives are added to conventional pressure-sensitive adhesives.
[0003]
For example, in the case of an acrylic pressure sensitive adhesive, the (meth) acrylic polymer itself is tacky and can be a pressure sensitive adhesive with good heat resistance and weather resistance without adding a tackifier. Compared to those added with an agent, it is inferior in adhesion at room temperature and adhesion to low energy surfaces such as polyolefin and automobile paint surfaces. Thus, the effective adhesion characteristic is provided by adding a tackifier.
[0004]
However, the improvement in adhesion properties brought about by the addition of such tackifiers is not always satisfactory. There is also a problem due to the addition of such tackifiers to acrylic pressure sensitive adhesives. When a general commercially available tackifier such as a rosin acid derivative is added to an acrylic pressure-sensitive adhesive, transparency and weather resistance are often lowered. Furthermore, when such a tackifier is present during the bulk polymerization reaction, it may act as a chain transfer agent or a reaction terminator depending on its structure, leading to inhibition or delay of the polymerization reaction.
[0005]
It is also known that an acrylic polymer is added as a tackifier to a pressure sensitive adhesive. For example, Japanese Patent Application Laid-Open No. 54-3136 discloses a pressure-sensitive adhesive containing an acrylic polymer and a tackifier. The tackifier used here is obtained by solution polymerization of a vinyl aromatic compound and a (meth) acrylic ester, has a number average molecular weight of 500 to 3000, and a softening point of 40 ° C. or less. It is. In contrast, JP-A-1-139665 discloses a (meth) acrylate having a C1-C20 alkyl group and a cycloalkyl group, a free radical-compatible olefinic acid (specifically acrylic acid, etc.), and An invention of an adhesive composition containing a polymer type additive having a number average molecular weight of 35,000 or less and a softening point of 40 ° C. or more obtained by polymerizing other ethylenically unsaturated monomers as desired is disclosed. ing. This publication describes that the polymer type additive can be produced by any of emulsion polymerization, turbid suspension polymerization, solution polymerization, and bulk polymerization. Further, this publication discloses that “this polymer type additive is added to the adhesive composition by a known method, for example, a mixing or blending method, so that the additive is uniformly contained in the adhesive composition. The additive is preferable. Is added to the pressure sensitive adhesive composition in the form of an emulsion or an emulsion in an aqueous / organic solvent combination solute. "
[0006]
However, in this publication, the polymer-type additive is produced by emulsion polymerization or solution polymerization, and is thus blended with the pressure-sensitive adhesive prepared by emulsion polymerization or solution polymerization in a state of being emulsified and dispersed or dissolved in the solute. Yes.
As described above, in the above publication, the pressure-sensitive adhesive and polymer type additive obtained by emulsion polymerization or solution polymerization are all used so far that an acrylic monomer can be polymerized without using a reaction solvent. Although known (bulk polymerization), the polymerization of acrylic monomers carried out without using such a reaction solvent is extremely difficult to control the reaction, and selectively produces a polymer having certain characteristics. Because it was not possible. In addition, the pressure-sensitive adhesive and polymer type additive produced by solution polymerization or emulsion polymerization are none other than being able to easily produce a uniform composition by mixing with a reaction solvent.
[0007]
However, when adhering using such a pressure-sensitive adhesive composition or emulsion-type pressure-sensitive adhesive composition containing a solvent, a process for removing the solvent is required. For example, when water having a large latent heat of vaporization is used. The drying process becomes very long. Moreover, when an organic solvent is used, there is a problem that an apparatus for capturing the diffused organic solvent is required, and there is a concern about the influence on the environment.
[0008]
On the other hand, as methods for producing a pressure-sensitive adhesive without using a solvent, there are JP-A-50-87129 and JP-A-50-102635, and these publications include alkyl (meth) acrylates. A pressure-sensitive property in which a mixture obtained by adding these (co) polymer and polymerization initiator to a mixture of an ester and a vinyl monomer having a specific polar group is applied to a support sheet and polymerized by heating. An adhesive tape manufacturing method is disclosed. In Japanese Patent Laid-Open No. 50-87129, redox type polymerization initiators are used because normal polymerization initiators do not proceed smoothly due to the inhibition of oxygen polymerization. In the -102635 publication, a release sheet or belt is stacked on a coated raw material pressure-sensitive adhesive composition, and contact with oxygen is cut off to cause a thermal polymerization reaction.
[0009]
Thus, by using (meth) acrylic acid alkyl ester as a solvent and blending an acrylic (co) polymer here, a tape having pressure-sensitive adhesiveness can be produced without using an organic solvent. .
However, in the method disclosed in the above publication, since the monomer used as the solvent is polymerized by heat polymerization, the surface portion of the coating layer that is likely to come into contact with oxygen in the air is always in contact with oxygen. There is a possibility that the reaction may be stopped by contact, and there is a problem that polymerization is difficult to proceed uniformly in the thickness direction of the layer. In addition, since the monomer used here needs to dissolve the (co) polymer, it has the same or similar composition as the solute (co) polymer. Therefore, the pressure-sensitive adhesive layer of the pressure-sensitive adhesive tape obtained by the method described in the above publication is formed from a (co) polymer having substantially the same composition.
[0010]
In such a pressure-sensitive adhesive layer made of a (co) polymer having a substantially single composition, sufficient adhesive strength is not exhibited with respect to an adherend which is considered difficult to adhere, such as polyolefin.
[0011]
OBJECT OF THE INVENTION
An object of this invention is to provide the novel acrylic adhesive composition which does not contain a solvent substantially.
In addition, the present invention can form an adhesive that exhibits very high adhesion even to adherends that are conventionally considered to be very difficult to adhere, such as polyolefin. An object of the present invention is to provide an acrylic pressure-sensitive adhesive composition having excellent coatability and curability.
[0012]
Furthermore, this invention aims at providing the adhesive tape using the above adhesive compositions, and its manufacturing method.
[0013]
SUMMARY OF THE INVENTION
The acrylic pressure-sensitive adhesive composition of the present invention is50% by weight or more of (meth) acrylic acid alkyl ester of (meth) acrylic acid and an alcohol having an alkyl group having 1 to 20 carbon atoms as a main constituent unitMonomer,By bulk polymerization without solventThe weight average molecular weight obtained by partial polymerization is 50,000 or more,Glass transition temperature is 0 to -85 ° CAdhesive polymer (a); 5-75 parts by weight, and(Meth) acrylic acid alkyl ester of (meth) acrylic acid which is an unreacted monomer at the time of partial polymerization by bulk polymerization without containing a solvent and an alcohol having an alkyl group having 1 to 20 carbon atoms. Monomer composed mainly of (meth) acrylic acid ester containing 50% by weight or more as a main structural unit(C); 20-90 parts by weight of the mixture;(Meth) acrylic acid and (meth) acrylic acid alkyl ester with an alcohol having an alkyl group having 1 to 4 carbon atoms, ester of (meth) acrylic acid with an alicyclic alcohol having 3 to 14 carbon atoms, (meth) A monomer having a polymerizable unsaturated bond containing 50% by weight or more of an ester of acrylic acid and an aromatic alcohol having 6 to 14 carbon atomsPolymerized andWithout using reaction solventInConversion rate was 100%The weight average molecular weight is 20000 or lessThe glass transition temperature is 40 to 180 ° C.Tackifying resin(b); 5 to 40 parts by weight are added and mixed;Contains no solventAnd an acrylic pressure-sensitive adhesive composition (provided that the total of component (a), component (b), and component (c) is 100 parts by weight).
[0014]
  In addition, the method for producing the pressure-sensitive adhesive tape of the present invention includes50% by weight or more of (meth) acrylic acid alkyl ester of (meth) acrylic acid and an alcohol having an alkyl group having 1 to 20 carbon atoms as a main constituent unitMonomer,By bulk polymerization without solventThe weight average molecular weight obtained by partial polymerization is 50,000 or more,Glass transition temperature is 0 to -85 ° CAdhesive polymer (a); 5-75 parts by weight, and(Meth) acrylic acid alkyl ester of (meth) acrylic acid which is an unreacted monomer at the time of partial polymerization by bulk polymerization without containing a solvent and an alcohol having an alkyl group having 1 to 20 carbon atoms. Monomer composed mainly of (meth) acrylic acid ester containing 50% by weight or more as a main structural unit(C); 20-90 parts by weight of the mixture;(Meth) acrylic acid and (meth) acrylic acid alkyl ester with an alcohol having an alkyl group having 1 to 4 carbon atoms, ester of (meth) acrylic acid with an alicyclic alcohol having 3 to 14 carbon atoms, (meth) A monomer having a polymerizable unsaturated bond containing 50% by weight or more of an ester of acrylic acid and an aromatic alcohol having 6 to 14 carbon atomsPolymerized andWithout using reaction solventInConversion rate was 100%The weight average molecular weight is 20000 or lessThe glass transition temperature is 40 to 180 ° C.Tackifying resin(b); 5 to 40 parts by weight are added and mixed;Contains no solventAcrylic pressure-sensitive adhesive composition (however, the total of component (a), component (b), and component (c) is 100 parts by weight) and 0.1 part by weight with respect to 100 parts by weight of the acrylic pressure-sensitive adhesive composition. A mixture with 01 to 3 parts by weight of a polymerization initiator is applied to the support surface at a thickness of 0.01 to 1.0 mm and then polymerized.
[0015]
  Furthermore, the adhesive tape of the present invention is50% by weight or more of (meth) acrylic acid alkyl ester of (meth) acrylic acid and an alcohol having an alkyl group having 1 to 20 carbon atoms as a main constituent unitMonomer,By bulk polymerization without solventThe weight average molecular weight obtained by partial polymerization is 50,000 or more,Glass transition temperature is 0 to -85 ° CAdhesive polymer (a); 5-75 parts by weight, and(Meth) acrylic acid alkyl ester of (meth) acrylic acid which is an unreacted monomer at the time of partial polymerization by bulk polymerization without containing a solvent and an alcohol having an alkyl group having 1 to 20 carbon atoms. Monomer composed mainly of (meth) acrylic acid ester containing 50% by weight or more as a main structural unit(C); 20-90 parts by weight of the mixture;(Meth) acrylic acid and (meth) acrylic acid alkyl ester with an alcohol having an alkyl group having 1 to 4 carbon atoms, ester of (meth) acrylic acid with an alicyclic alcohol having 3 to 14 carbon atoms, (meth) A monomer having a polymerizable unsaturated bond containing 50% by weight or more of an ester of acrylic acid and an aromatic alcohol having 6 to 14 carbon atomsPolymerized andWithout using reaction solventInConversion rate was 100%The weight average molecular weight is 20000 or lessThe glass transition temperature is 40 to 180 ° C.Tackifying resin(b); 5 to 40 parts by weight are added and mixed;Contains no solventAcrylic pressure-sensitive adhesive composition (however, the total of component (a), component (b), and component (c) is 100 parts by weight) and 0.1 part by weight with respect to 100 parts by weight of the acrylic pressure-sensitive adhesive composition. The pressure-sensitive adhesive tape is obtained by polymerizing a mixture of 0.01 to 3 parts by weight of a polymerization initiator on the surface of a support with a thickness of 0.01 to 1.0 mm, and then polymerizing the mixture.
[0016]
The acrylic pressure-sensitive adhesive composition of the present invention has a low glass transition temperature, a weight-average molecular weight having adhesiveness at room temperature of 50000 or more, (a) a pressure-sensitive polymer, and a glass transition temperature higher than room temperature. Although it does not have tackiness, it can be imparted to this composition by adding to the pressure-sensitive adhesive composition, and comprises (b) a tackifying resin and (c) a monomer. A pressure-sensitive adhesive having high adhesive strength can be produced, for example, by adding a polymerization initiator to the pressure-sensitive adhesive composition for polymerization. In particular, the acrylic pressure-sensitive adhesive composition of the present invention has a low affinity with the pressure-sensitive adhesive, and exhibits an excellent pressure-sensitive adhesive property even when pasted on a polyolefin that is difficult to bond.
[0017]
A pressure-sensitive adhesive tape can be produced by applying the acrylic pressure-sensitive adhesive composition of the present invention to the surface of a support and polymerizing the composition on the support. And this acrylic adhesive composition contains a low molecular weight tackifier resin having a high glass transition temperature, and the resulting adhesive tape is higher than the conventional adhesive tape by the addition of this tackifier resin. Has peel strength. In addition, since this acrylic pressure-sensitive adhesive composition does not contain a solvent, there is no need for a process for removing the solvent during tape production, and the tape can be produced in a short process, and the environment is also contaminated by the solvent. Does not occur.
[0018]
DETAILED DESCRIPTION OF THE INVENTION
Next, the pressure-sensitive adhesive composition, pressure-sensitive adhesive tape and production method thereof of the present invention will be specifically described.
In the acrylic pressure-sensitive adhesive composition of the present invention,
(a) High molecular weight adhesive polymer
(b) Low molecular weight tackifying resin
and
(c) A monomer is contained.
[0019]
The (a) high molecular weight adhesive polymer constituting the acrylic adhesive composition of the present invention is an adhesive polymer having a (meth) acrylic acid ester component unit as a main constituent unit and a weight average molecular weight of 50,000 or more.
This (a) adhesive polymer has adhesiveness at room temperature, and the glass transition temperature of this (a) adhesive polymer is usually 0 ° C. or lower, preferably in the range of 0 ° C. to −85 ° C. is there. When this (a) adhesive polymer has such a glass transition temperature, the adhesive obtained using the composition of the present invention has a basic adhesive force. Moreover, the weight average molecular weight of this (a) adhesive polymer is 50000 or more, and it is preferable that it exists in the range of 100,000-2 million. If the weight average molecular weight of this (a) adhesive polymer is less than 50000, sufficient adhesive performance is not exhibited in the adhesive obtained using the composition of the present invention. In the present invention, the weight average molecular weight is a value determined by gel permeation chromatography (GPC).
[0020]
This (a) high molecular weight adhesive polymer is formed by polymerizing a monomer having a polymerizable unsaturated bond mainly composed of (meth) acrylic acid ester.
In the present invention, as such (meth) acrylic acid ester, (meth) acrylic acid alkyl ester of (meth) acrylic acid and an alcohol having an alkyl group having 1 to 20 carbon atoms, (meth) acrylic acid and 3 to 3 carbon atoms. An ester of 14 alicyclic alcohol and an ester of (meth) acrylic acid and an aromatic alcohol having 6 to 14 carbon atoms can be used.
[0021]
Examples of such (meth) acrylic acid esters include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, pentyl (meth) acrylate, ( (Meth) acrylic such as hexyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, octyl (meth) acrylate, nonyl (meth) acrylate, decyl (meth) acrylate, dodecyl (meth) acrylate Acid alkyl esters;
Esters of (meth) acrylic acid with cycloaliphatic alcohols such as cyclohexyl (meth) acrylate;
Mention may be made of (meth) acrylic acid aryl esters such as phenyl (meth) acrylate and benzyl (meth) acrylate. Such (meth) acrylic acid esters can be used alone or in combination.
[0022]
The (a) high molecular weight adhesive polymer used in the present invention is prepared using the (meth) acrylic acid ester as a main component as a monomer having a polymerizable unsaturated bond. Therefore, the (a) high molecular weight adhesive polymer used in the present invention is a monomer conversion of a repeating unit ((meth) acrylic acid ester component unit) derived from the (meth) acrylic acid ester as described above. In an amount of 50% by weight or more, preferably 70% by weight or more, and more preferably 90% by weight or more.
[0023]
The (a) high molecular weight adhesive polymer used in the present invention is a repeating unit derived from a monomer copolymerizable with (meth) acrylic acid ester in addition to the above (meth) acrylic acid ester component unit. You may have.
Examples of such monomers include
(Meth) acrylic acid,
Alkoxyalkyl (meth) acrylates such as methoxyethyl (meth) acrylate, ethoxyethyl (meth) acrylate, propoxyethyl (meth) acrylate, butoxyethyl (meth) acrylate, ethoxypropyl (meth) acrylate;
Salts such as alkali metal salts of (meth) acrylic acid;
Di (meth) acrylic acid ester of ethylene glycol, di (meth) acrylic acid ester of diethylene glycol, di (meth) acrylic acid ester of triethylene glycol, di (meth) acrylic acid ester of polyethylene glycol, di (meta) of propylene glycol ) Di (meth) acrylates of (poly) alkylene glycols such as acrylates, di (meth) acrylates of dipropylene glycol, di (meth) acrylates of tripropylene glycol;
Polyvalent (meth) acrylates such as trimethylolpropane tri (meth) acrylate;
(Meth) acrylonitrile; vinyl acetate; vinylidene chloride;
Halogenated vinyl compounds such as (meth) acrylic acid-2-chloroethyl;
Oxazoline group-containing polymerizable compounds such as 2-vinyl-2-oxazoline, 2-vinyl-5-methyl-2-oxazoline, 2-isopropenyl-2-oxazoline;
Aziridine group-containing polymerizable compounds such as (meth) acryloylaziridine and (meth) acrylic acid-2-aziridinylethyl;
Epoxy group-containing vinyl monomers such as allyl glycidyl ether, (meth) acrylic acid glycidyl ether, (meth) acrylic acid glycidyl ether, (meth) acrylic acid-2-ethylglycidyl ether;
(Meth) acrylic acid-2-hydroxyethyl, acrylic acid-2-hydroxypropyl, monoester of (meth) acrylic acid and polypropylene glycol or polyethylene glycol, lactones and (meth) acrylic acid-2-hydroxyethyl Hydroxyl group-containing vinyl compounds such as adducts;
Fluorine-containing vinyl monomers such as fluorine-substituted methacrylic acid alkyl ester and fluorine-substituted alkyl acrylate;
Unsaturated carboxylic acids such as itaconic acid, crotonic acid, maleic acid, fumaric acid (excluding (meth) acrylic acid), their salts and their (partial) ester compounds and acid anhydrides;
Reactive halogen-containing vinyl monomers such as 2-chloroethyl vinyl ether and monochloro vinyl acetate;
Amide group-containing vinyl monomers such as methacrylamide, N-methylol methacrylamide, N-methoxyethyl methacrylamide, N-butoxymethyl methacrylamide;
Organosilicon group-containing vinyl compound monomers such as vinyltrimethoxysilane, γ-methacryloxypropyltrimethoxysilane, allyltrimethoxysilane, trimethoxysilylpropylallylamine, 2-methoxyethoxytrimethoxysilane;
Other examples include macromonomer having a radical polymerizable vinyl group at the terminal of the monomer obtained by polymerizing vinyl group (for example, fluorine-based monomer, silicon-containing monomer, macromonomer, styrene, silicon, etc.). Such monomers can be copolymerized with the (meth) acrylic acid ester alone or in combination.
[0024]
Examples of (a) high molecular weight adhesive polymers used in the present invention include copolymers of butyl acrylate / 2-ethylhexyl acrylate / acrylic acid / 2-hydroxyethyl acrylate, 2-ethylhexyl acrylate / acrylic acid / 2- Mention may be made of copolymers of hydroxyethyl acrylate.
The (b) low molecular weight tackifying resin that forms the acrylic pressure-sensitive adhesive composition of the present invention is solid without stickiness at room temperature. The glass transition temperature of the (b) low molecular weight tackifying resin is usually 40 ° C. or higher, preferably 40 ° C. to 180 ° C. By blending this (b) low molecular weight tackifier resin, the adhesive performance of the adhesive tape of the present invention is remarkably improved. The weight average molecular weight of the (b) low molecular weight tackifying resin is 20000 or less, preferably 10,000 or less, and particularly preferably in the range of 10,000 to 2,000. When the weight average molecular weight of the (b) low molecular weight tackifying resin exceeds 20000, the effect of improving the adhesive performance in the adhesive obtained by using the composition of the present invention is not sufficiently exhibited.
[0025]
This (b) low molecular weight tackifier resin is formed by polymerizing a monomer having a polymerizable unsaturated bond mainly composed of (meth) acrylic acid ester.
In the present invention, as such (meth) acrylic acid ester, (meth) acrylic acid alkyl ester of (meth) acrylic acid and an alcohol having 1 to 20 carbon atoms, preferably 1 to 4 alkyl groups, (meth) acrylic. An ester of an acid and an alicyclic alcohol having 3 to 14 carbon atoms, or an ester of (meth) acrylic acid and an aromatic alcohol having 6 to 14 carbon atoms can be used.
[0026]
Examples of such (meth) acrylic acid esters include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, pentyl (meth) acrylate, ( (Meth) acrylic such as hexyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, octyl (meth) acrylate, nonyl (meth) acrylate, decyl (meth) acrylate, dodecyl (meth) acrylate Acid alkyl esters;
Esters of (meth) acrylic acid with cycloaliphatic alcohols such as cyclohexyl (meth) acrylate;
Mention may be made of (meth) acrylic acid aryl esters such as phenyl (meth) acrylate and benzyl (meth) acrylate. Such (meth) acrylic acid esters can be used alone or in combination. Among such (meth) acrylic acid esters, in the present invention, (meth) acrylic acid alkyl ester having an alkyl group having 1 to 4 carbon atoms and / or an alicyclic alcohol having 3 to 14 carbon atoms and (meta ) An ester with acrylic acid and / or an ester with benzyl alcohol is used.
[0027]
The (b) low molecular weight tackifier resin used in the present invention is prepared using the (meth) acrylic acid ester as a main component as a monomer having a polymerizable unsaturated bond. Therefore, the (b) low molecular weight tackifying resin used in the present invention is a monomer comprising a repeating unit ((meth) acrylic acid ester component unit) derived from the (meth) acrylic acid ester as described above. In terms of conversion, it is contained in an amount of 50% by weight or more, preferably 70% by weight or more, and more preferably 90% by weight or more.
[0028]
The (b) low molecular weight tackifying resin used in the present invention is a repeating product derived from a monomer copolymerizable with (meth) acrylic acid ester in addition to the above (meth) acrylic acid ester component unit. You may have a unit.
Examples of such monomers include
(Meth) acrylic acid,
Alkoxyalkyl (meth) acrylates such as methoxyethyl (meth) acrylate, ethoxyethyl (meth) acrylate, propoxyethyl (meth) acrylate, butoxyethyl (meth) acrylate, ethoxypropyl (meth) acrylate;
Salts such as alkali metal salts of (meth) acrylic acid;
Di (meth) acrylic acid ester of ethylene glycol, di (meth) acrylic acid ester of diethylene glycol, di (meth) acrylic acid ester of triethylene glycol, di (meth) acrylic acid ester of polyethylene glycol, di (meta) of propylene glycol ) Di (meth) acrylates of (poly) alkylene glycols such as acrylates, di (meth) acrylates of dipropylene glycol, di (meth) acrylates of tripropylene glycol;
Polyvalent (meth) acrylates such as trimethylolpropane tri (meth) acrylate;
(Meth) acrylonitrile; vinyl acetate; vinylidene chloride;
Halogenated vinyl compounds such as (meth) acrylic acid-2-chloroethyl;
Oxazoline group-containing polymerizable compounds such as 2-vinyl-2-oxazoline, 2-vinyl-5-methyl-2-oxazoline, 2-isopropenyl-2-oxazoline;
Aziridine group-containing polymerizable compounds such as (meth) acryloylaziridine and (meth) acrylic acid-2-aziridinylethyl;
Epoxy group-containing vinyl monomers such as allyl glycidyl ether, (meth) acrylic acid glycidyl ether, (meth) acrylic acid glycidyl ether, (meth) acrylic acid-2-ethylglycidyl ether;
(Meth) acrylic acid-2-hydroxyethyl, acrylic acid-2-hydroxypropyl, monoester of (meth) acrylic acid and polypropylene glycol or polyethylene glycol, lactones and (meth) acrylic acid-2-hydroxyethyl Hydroxyl group-containing vinyl compounds such as adducts;
Fluorine-containing vinyl monomers such as fluorine-substituted methacrylic acid alkyl ester and fluorine-substituted alkyl acrylate;
Unsaturated carboxylic acids such as itaconic acid, crotonic acid, maleic acid, fumaric acid (excluding (meth) acrylic acid), their salts and their (partial) ester compounds and acid anhydrides;
Reactive halogen-containing vinyl monomers such as 2-chloroethyl vinyl ether and monochloro vinyl acetate;
Amide group-containing vinyl monomers such as methacrylamide, N-methylol methacrylamide, N-methoxyethyl methacrylamide, N-butoxymethyl methacrylamide;
Organosilicon group-containing vinyl compound monomers such as vinyltrimethoxysilane, γ-methacryloxypropyltrimethoxysilane, allyltrimethoxysilane, trimethoxysilylpropylallylamine, 2-methoxyethoxytrimethoxysilane;
Other examples include macromonomer having a radical polymerizable vinyl group at the terminal of the monomer obtained by polymerizing vinyl group (for example, fluorine-based monomer, silicon-containing monomer, macromonomer, styrene, silicon, etc.). Such monomers can be copolymerized with the (meth) acrylic acid ester alone or in combination.
[0029]
Furthermore, it is preferable that a functional group having reactivity with an epoxy group or an isocyanate group is introduced into the (b) low molecular weight tackifying resin. Examples of such functional groups include hydroxyl groups, carboxyl groups, amino groups, amide groups, mercapto groups, and (b) monomers having such functional groups when producing low molecular weight tackifying resins. It is preferable to use it. Usually, the (b) low molecular weight tackifying resin has a composition different from that of the (a) high molecular weight tackifying polymer. Further, the monomer that forms the low molecular weight tackifying resin (b) and the monomer (c) have different compositions. However, the (b) low molecular weight tackifying resin and the monomer (c) have a common unit called (meth) acrylic acid ester. Dissolve.
[0030]
Examples of the (b) low molecular weight tackifying resin used in the present invention include a copolymer of isobutyl methacrylate and methacrylic acid.
The acrylic pressure-sensitive adhesive composition of the present invention mainly comprises (c) (meth) acrylic acid ester in addition to (a) high molecular weight pressure-sensitive adhesive polymer and (b) low molecular weight tackifier resin as described above. Contains monomer as a component.
[0031]
The monomer comprising the (c) (meth) acrylic acid ester as the main component constituting the acrylic pressure-sensitive adhesive composition of the present invention dissolves the above (a) high molecular weight adhesive polymer and (b) low molecular weight tackifier resin. Alternatively, while being dispersed, the monomer (c) is copolymerized to form an adhesive.
Examples of such monomers having (c) (meth) acrylate as a main component include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, and butyl (meth) acrylate. , Pentyl (meth) acrylate, hexyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, octyl (meth) acrylate, nonyl (meth) acrylate, decyl (meth) acrylate, (meth) acryl (Meth) acrylic acid alkyl esters such as dodecyl acid;
Esters of (meth) acrylic acid with cycloaliphatic alcohols such as cyclohexyl (meth) acrylate;
Mention may be made of (meth) acrylic acid aryl esters such as phenyl (meth) acrylate and benzyl (meth) acrylate. Such (meth) acrylic acid esters can be used alone or in combination.
[0032]
The monomer having (c) (meth) acrylic acid ester as the main component used in the present invention is mainly composed of the above (meth) acrylic acid ester, but may further contain other monomers. . Examples of other monomers that can be used in the present invention include:
(Meth) acrylic acid,
Alkoxyalkyl (meth) acrylates such as methoxyethyl (meth) acrylate, ethoxyethyl (meth) acrylate, propoxyethyl (meth) acrylate, butoxyethyl (meth) acrylate, ethoxypropyl (meth) acrylate;
Salts such as alkali metal salts of (meth) acrylic acid;
Di (meth) acrylic acid ester of ethylene glycol, di (meth) acrylic acid ester of diethylene glycol, di (meth) acrylic acid ester of triethylene glycol, di (meth) acrylic acid ester of polyethylene glycol, di (meta) of propylene glycol ) Di (meth) acrylates of (poly) alkylene glycols such as acrylates, di (meth) acrylates of dipropylene glycol, di (meth) acrylates of tripropylene glycol;
Polyvalent (meth) acrylates such as trimethylolpropane tri (meth) acrylate;
(Meth) acrylonitrile; vinyl acetate; vinylidene chloride;
Halogenated vinyl compounds such as (meth) acrylic acid-2-chloroethyl;
(Meth) acrylic acid esters of alicyclic alcohols such as (meth) acrylic acid cyclohexyl;
Oxazoline group-containing polymerizable compounds such as 2-vinyl-2-oxazoline, 2-vinyl-5-methyl-2-oxazoline, 2-isopropenyl-2-oxazoline;
Aziridine group-containing polymerizable compounds such as (meth) acryloylaziridine and (meth) acrylic acid-2-aziridinylethyl;
Epoxy group-containing vinyl monomers such as allyl glycidyl ether, (meth) acrylic acid glycidyl ether, (meth) acrylic acid glycidyl ether, (meth) acrylic acid-2-ethylglycidyl ether;
(Meth) acrylic acid-2-hydroxyethyl, acrylic acid-2-hydroxypropyl, monoester of (meth) acrylic acid and polypropylene glycol or polyethylene glycol, lactones and (meth) acrylic acid-2-hydroxyethyl Hydroxyl group-containing vinyl compounds such as adducts;
Fluorine-containing vinyl monomers such as fluorine-substituted methacrylic acid alkyl ester and fluorine-substituted alkyl acrylate;
Unsaturated carboxylic acids such as itaconic acid, crotonic acid, maleic acid, fumaric acid (excluding (meth) acrylic acid), their salts and their (partial) ester compounds and acid anhydrides;
Reactive halogen-containing vinyl monomers such as 2-chloroethyl vinyl ether and monochloro vinyl acetate;
Amide group-containing vinyl monomers such as methacrylamide, N-methylol methacrylamide, N-methoxyethyl methacrylamide, N-butoxymethyl methacrylamide;
Organosilicon group-containing vinyl compound monomers such as vinyltrimethoxysilane, γ-methacryloxypropyltrimethoxysilane, allyltrimethoxysilane, trimethoxysilylpropylallylamine, 2-methoxyethoxytrimethoxysilane;
Other examples include macromonomer having a radical polymerizable vinyl group at the terminal of the monomer obtained by polymerizing vinyl group (for example, fluorine-based monomer, silicon-containing monomer, macromonomer, styrene, silicon, etc.). Such monomers can be copolymerized with the (meth) acrylic acid ester alone or in combination.
[0033]
However, in the present invention, the monomer is mainly composed of (meth) acrylic acid ester. Therefore, (meth) acrylic acid ester is 50% by weight or more, preferably 70% by weight or more, more preferably 90% by weight or more. It is contained in the amount.
The acrylic pressure-sensitive adhesive composition of the present invention contains the above (a) high molecular weight adhesive polymer in an amount of 5 to 75 parts by weight, and (b) 5 to 40 parts by weight of a low molecular weight tackifier resin. (C) the monomer is contained in an amount of 20 to 90 parts by weight. However, in the present invention, the total of the components (a), (b) and (c) is 100 parts by weight.
[0034]
The acrylic pressure-sensitive adhesive composition of the present invention having the composition as described above is obtained by dissolving or dispersing the component (a) and the component (b) in the monomer as the component (c), so that a so-called solvent is substantially contained. Not contained in. And when the viscosity in 25 degreeC is measured about the acrylic adhesive composition of this invention which has the said composition, it is a viscous liquid which has a viscosity within the range of 1000-100000 cps normally, Preferably it is 3000-50000 cps. A liquid having such a viscosity can be coated on a support using a normal coating apparatus.
[0035]
  Acrylic pressure-sensitive adhesive composition of the present invention(A) componentIt is preferable to produce a mixture of the component (a) and the component (c) by partially polymerizing the monomer forming the component, and add and mix the component (b) separately produced in the mixture. .
[0036]
A partial polymer obtained by polymerizing a monomer having a polymerizable unsaturated bond mainly composed of an acrylic alkyl ester by bulk polymerization is a viscous liquid containing a component (a) and a component (c). Contains no solvent.
The (b) low molecular weight tackifying resin used in the present invention can be produced by various methods. However, it is possible to use a resin obtained by further polymerizing a partial polymer to make the polymerization rate substantially 100%. preferable. This (b) low molecular weight tackifying resin also contains no solvent. As a method of controlling the weight average molecular weight within the range specified in the present invention when (b) producing a low molecular weight tackifying resin using such a method, the amount of polymerization initiator is adjusted, or the reaction Set the temperature higher or use a larger amount of chain transfer agent than is generally used.
[0037]
The acrylic pressure-sensitive adhesive composition of the present invention contains the above-mentioned components (a), (b) and (c), and such a composition is polymerized by, for example, irradiation with an electron beam. be able to. However, since the acrylic pressure-sensitive adhesive composition of the present invention exhibits excellent adhesiveness by polymerizing the contained monomer, it is preferable to blend a polymerization initiator in this composition. Examples of the polymerization initiator used here include a thermal polymerization initiator and a photopolymerization initiator. In particular, the acrylic pressure-sensitive adhesive composition of the present invention is preferably applied to the support surface and irradiated with energy rays such as ultraviolet rays to form a pressure-sensitive adhesive. Therefore, in the acrylic pressure-sensitive adhesive composition of the present invention, It is preferable to mix a photopolymerization initiator.
[0038]
The photopolymerization initiator is usually from 0.01 to 3 parts by weight, preferably from 0.05 to 2 parts by weight, based on a total of 100 parts by weight of the components (a), (b) and (c). It is blended in an amount within the range.
The photopolymerization initiator used in the present invention is a photoradical polymerization initiator and / or a photocationic polymerization initiator, and examples thereof include 4- (2-hydroxyethoxy) phenyl (2-hydroxy-2-). Propyl) ketone [for example, Ciba Geigy, trade name: Darocur 2959], α-hydroxy-α, α′-dimethylacetophenone [for example, Ciba Geigy, trade name: Darocur 1173], methoxyacetophenone, 2,2-dimethoxy-2 -Acetophenone photopolymerization initiators such as phenylacetone [for example, Ciba Geigy, trade name: Irgacure 651], 2-hydroxy-2-cyclohexylacetophenone [Ciba Geigy, trade name: Irgacure 184]; benzyldimethyl ketal, etc. Ketal photopolymerization initiators; other halogenated ketones, acyl phosphinoxides, acyl A photopolymerization initiator such as ruphosphanate can be mentioned.
[0039]
Moreover, it is preferable to mix | blend a crosslinking agent with the acrylic adhesive composition of this invention.
The cross-linking agent used in the present invention is a compound that can form a cross-linked structure between components formed by polymerization of the component (a), the component (b), and the component (c).
This crosslinking agent is usually in the range of 0.01 to 5 parts by weight, preferably 0.01 to 3 parts by weight with respect to 100 parts by weight of the total of the components (a), (b) and (c). It is blended in the amount of.
[0040]
Examples of such crosslinking agents include compounds having an epoxy group and compounds having an isocyanate group. Specifically, compounds having an epoxy group include bisphenol A, epichlorohydrin type epoxy resin, ethylene glycidyl ether, polyethylene glycol diglycidyl ether, glycerin diglycidyl ether, glycerin triglycidyl ether, 1,6-hexanediol glycidyl. Ether, trimethylolpropane triglycidyl ether, diglycidyl aniline, diamine glycidyl amine, N, N, N ', N'-tetraglycidyl-m-xylylenediamine and 1,3-bis (N, N'-diamine glycidylamino) Methyl) cyclohexane and the like. Examples of isocyanate compounds include tolylene diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, xylylene diisocyanate, hydrogenated xylylene. Diisocyanate, diphenylmethane diisocyanate, hydrogenated diphenylmethane diisocyanate, tetramethyl xylylene diisocyanate, may be mentioned naphthalene diisocyanate, triphenylmethane triisocyanate, an adduct of a polymethylene polyphenyl isocyanate and polyol, such as those trimethylolpropane.
[0041]
In addition, when using the said polymerization initiator and a crosslinking agent, it is preferable that these also contain a solvent substantially.
The acrylic pressure-sensitive adhesive composition of the present invention further includes, as a filler, inorganic materials such as calcium carbonate, aluminum hydroxide, silica, clay, talc, and titanium oxide, and inorganic hollow bodies such as glass balloons, shirasu balloons, and ceramic balloons. Additives that are usually added to adhesives such as organic substances such as nylon beads, acrylic beads, silicone beads, organic hollow bodies such as vinylidene chloride balloons, acrylic balloons, foaming agents, dyes, pigments, polymerization inhibitors, stabilizers, etc. May be.
[0042]
By applying the acrylic pressure-sensitive adhesive composition of the present invention to the surface of a support and polymerizing it, a pressure-sensitive adhesive tape having a good pressure-sensitive adhesive can be produced.
Examples of the support used here include polyolefin film, polyester film, paper, metal foil, cloth, nonwoven fabric, silicone-treated polyester film, and silicone-treated paper.
[0043]
The acrylic pressure-sensitive adhesive composition of the present invention is applied to such a support surface. The coating thickness of this composition is 0.01 to 1.0 mm.
Thus, the pressure-sensitive adhesive layer can be formed by polymerizing the acrylic pressure-sensitive adhesive composition applied to the surface of the support. The method for forming this pressure-sensitive adhesive layer varies depending on the polymerization initiator compounded in the composition. That is, for example, when a thermal polymerization initiator is blended, a pressure-sensitive adhesive layer is formed by heating, and when a photopolymerization initiator is blended, the polymerization reaction is caused by irradiation with energy rays such as ultraviolet rays. It progresses and an adhesive layer is formed. In particular, in the present invention, it is preferable to apply an acrylic pressure-sensitive adhesive composition containing a radical photopolymerization initiator to the surface of the support, and to polymerize the thus formed coating layer by irradiating with ultraviolet rays. In such a case, the irradiation time of ultraviolet rays varies depending on the thickness of the coating layer, but is usually 10 seconds to 5 minutes, preferably 30 seconds to 3 minutes.
[0044]
For example, when the ultraviolet ray is irradiated as described above, the component (c) contained in the coating layer is polymerized, and when a crosslinking agent is further blended, a crosslinked structure is formed. Usually, by irradiating with ultraviolet rays or the like as described above, almost all of the blended component (c) is polymerized. Therefore, the pressure-sensitive adhesive layer contains substantially no monomer.
[0045]
By polymerizing in this way, in the pressure-sensitive adhesive layer of the pressure-sensitive adhesive tape of the present invention, (a) a high-molecular-weight pressure-sensitive polymer and (b) a low-molecular-weight tackifier resin, ) Each state is contained in the polymerized component while being almost maintained. Therefore, the (co) polymer consisting of the component (a), the component (b), and the component (c) maintains their excellent properties, but these three parties work together in a single composition. To develop characteristics that cannot be achieved. The outstanding effect of the adhesive obtained by using the composition of the present invention is to exhibit excellent adhesive strength to adherends which have been conventionally difficult to bond, such as polyolefin, particularly polypropylene. That is, the polyolefin has a low affinity with the adhesive, and when the polyolefin and another adherend are bonded via the adhesive layer, the adhesive strength at the interface between the adhesive layer and the polyolefin is usually the lowest. This is one of the most different points of polyolefin from other synthetic resins. However, an adhesive formed using the acrylic pressure-sensitive adhesive composition of the present invention has a markedly improved adhesive strength with such a polyolefin by blending (b) a low molecular weight tackifying resin. This (b) low molecular weight tackifying resin has a glass transition temperature of 40 ° C. or higher, and this (b) low molecular weight tackifying resin is blended at room temperature even though it does not have tackiness. By doing so, the adhesive strength to polyolefin is improved by 2 times or more as compared with the case where (b) the low molecular weight tackifying resin is not blended.
[0046]
That is, the pressure-sensitive adhesive tape of the present invention produced in this way exhibits good adhesion to polyolefins, particularly polyethylene, polypropylene, etc., which have been difficult to bond firmly conventionally. For example, the pressure-sensitive adhesive tape of the present invention with respect to polypropylene usually exhibits an adhesive strength (180 degree peel strength) of 1000 g / 20 mm or more.
[0047]
【The invention's effect】
The acrylic pressure-sensitive adhesive composition of the present invention comprises (a) a high molecular weight pressure-sensitive adhesive polymer and (c) a monomer mainly composed of (meth) acrylic acid ester, and (b) a low molecular weight tackifying resin. A pressure-sensitive adhesive tape, which is contained in a specific ratio and obtained by polymerizing this composition on a support and irradiating it with ultraviolet rays, for example, exhibits very high adhesive strength. In particular, the pressure-sensitive adhesive obtained from the composition of the present invention is excellent in adhesiveness to polyolefins that have been difficult to bond, and has excellent curability when used as a pressure-sensitive adhesive tape.
[0048]
Furthermore, the said adhesiveness improves further by mix | blending a crosslinking agent with the acrylic adhesive composition of this invention, and preparing an adhesive.
In addition, the acrylic pressure-sensitive adhesive composition of the present invention does not substantially contain a solvent, and does not require a solvent removal step when producing the pressure-sensitive adhesive, and there is no environmental contamination due to the solvent. Further, the acrylic pressure-sensitive adhesive composition of the present invention does not contain a solvent as described above, and the pressure-sensitive adhesive obtained from this composition does not contain a solvent. In particular, it does not contain low-boiling substances. For this reason, there are few off-flavors, such as a residual organic solvent odor peculiar to the conventional adhesive.
[0049]
【Example】
Next, although the acrylic adhesive composition and adhesive tape of this invention are demonstrated concretely, this invention is not specifically limited by these.
Preparation of adhesive polymer 1 Partial polymerization syrup A
In a two-liter four-necked flask equipped with a stirrer, thermometer, nitrogen gas inlet tube and cooling tube, 700 g of butyl acrylate (BA) and 255 g of 2-ethylhexyl acrylate (2-EHA) as polymerizable monomers Then, 40 g of acrylic acid (AA) and 5 g of 2-hydroxyethyl acrylate (2-HEA) were added, and 0.2 g of n-dodecyl mercaptan (NDM) was added as a molecular weight regulator, under a nitrogen stream. The temperature was raised to 60 ° C. and heating was stopped.
[0050]
Next, 0.2 g of azobisisobutyronitrile as a polymerization initiator was added with stirring, and the reaction was performed for 30 minutes to obtain partially polymerized syrup A.
The obtained partially polymerized syrup A was a viscous resin liquid having a polymer content of 22% by weight and a viscosity of 50 poise. Therefore, this partial polymer contains 78% by weight of residual monomer.
[0051]
The produced copolymer was separated from the partially polymerized syrup A thus obtained, and the weight average molecular weight (Mw) of this copolymer was measured by gel permeation chromatography (GPC). It was. Moreover, the glass transition temperature (Tg) of this copolymer was -59 degreeC.
Preparation of adhesive polymer 2 Partial polymerization syrup B
In a four-necked flask with a capacity of 2 liters equipped with a stirrer, thermometer, nitrogen gas inlet tube and cooling tube, 915 g of 2-ethylhexyl acrylate (2-EHA) and 80 g of acrylic acid (AA) as polymerizable monomers And 5 g of 2-hydroxyethyl acrylate (2-HEA) were added, and 0.1 g of n-dodecyl mercaptan (NDM) was added as a molecular weight regulator, and the temperature was raised to 60 ° C. under a nitrogen stream. The heating was stopped.
[0052]
Next, 0.2 g of azobisisobutyronitrile as a polymerization initiator was added with stirring, and the reaction was performed for 30 minutes to obtain partially polymerized syrup B.
The obtained partially polymerized syrup B was a viscous resin liquid having a polymer content of 25% by weight and a viscosity of 90 poise. Therefore, this partial polymer contains 75% by weight of residual monomer.
[0053]
The produced copolymer was separated from the thus obtained partially polymerized syrup B, and the Mw of this copolymer was measured by GPC, which was 690000. Moreover, the glass transition temperature (Tg) of this copolymer was -77 degreeC.
Preparation of tackifying resin
A tackifying resin having the composition and physical properties shown in Table 1 was prepared by further polymerizing using a partially polymerized syrup prepared by the same method as the above-mentioned adhesive polymer, so that the polymerization rate was 100%. .
[0054]
[Table 1]
[0055]
Examples 1-8
The tackifying resin was added to and mixed with the partially polymerized syrups A and B in the formulation shown in Table 2 to prepare the solventless acrylic pressure-sensitive adhesive composition of the present invention. To this composition, 0.5 part by weight of benzophenone as a photopolymerization initiator and an isocyanate-based crosslinking agent or an epoxy crosslinking agent were added to 100 parts by weight of this composition and mixed uniformly.
[0056]
This mixture was applied to the surface of the polyester film at a thickness of 0.05 mm and polymerized by irradiating with ultraviolet rays for 1 minute to produce the pressure-sensitive adhesive tape of the present invention.
About the obtained adhesive tape, the retention strength and the 180 degree | times peeling adhesive force with respect to polypropylene (PP) were measured.
[0057]
[Comparative Examples 1 and 2]
Except not having added tackifying resin, the adhesive tape was manufactured similarly to Examples 1-8, and the retention strength and the 180 degree | times peeling adhesive force with respect to PP were measured.
[0058]
[Comparative Example 3]
An adhesive tape was produced in the same manner as in Examples 1 to 8, except that a rosin acid derivative was used as the tackifying resin.
[0059]
[Comparative Examples 4-6]
A solventless acrylic pressure-sensitive adhesive composition outside the scope of the present invention was prepared, and a pressure-sensitive adhesive tape was produced in the same manner as in the above examples. The holding power and 180-degree peel adhesive strength against PP were measured.
Preparation of adhesive polymer 3 Partial polymerization syrup C
In the same manner as in partially polymerized syrup A, the weight ratio of the polymerizable monomer was butyl acrylate (BA) / 2-ethylhexyl acrylate (2-EHA) / acrylic acid (AA) / 2-hydroxyethyl acrylate (2-HEA ) = 70 / 25.5 / 4 / 0.5 partially polymerized syrup C was prepared. This partially polymerized syrup C was a viscous resin liquid having a polymer content of 30% and a viscosity of 2 poise. Moreover, the produced | generated polymer part was the weight average molecular weight (Mw) 46000, and the glass transition temperature (Tg) -59 degreeC.
[0060]
The results of Examples 1 to 8 and Comparative Examples 1 to 6 are shown in Tables 2 and 3. The adhesive strength and holding strength were measured by the following methods.
<Adhesive strength>
Using each adhesive tape, 180 degree peeling adhesive strength (g / 20 mm width) was measured using a polypropylene plate as an adherend in accordance with JIS Z 0237.
<Retention force>
Using each adhesive tape, stick one end of the adhesive tape to the SUS plate so that the adhesion area is 20 mm x 20 mm, and then press and reciprocate once with a 2 kg roller and leave it in an atmosphere of 80 ° C for 20 minutes. A 1 kg weight was attached to the other end of the tape, and the drop time or the shift distance after 1 hour was measured.
[0061]
[Table 2]
[0062]
[Table 3]

Claims (20)

  1.   A monomer containing 50% by weight or more of (meth) acrylic acid alkyl ester of (meth) acrylic acid and an alcohol having an alkyl group having 1 to 20 carbon atoms as a main constituent unit is partially polymerized by bulk polymerization not containing a solvent. The tacky polymer (a) having a weight average molecular weight of 50,000 or more and a glass transition temperature of 0 to −85 ° C .; 5 to 75 parts by weight of the monomer and the above monomer by bulk polymerization without containing a solvent. (Meth) containing 50% by weight or more of (meth) acrylic acid alkyl ester of (meth) acrylic acid, which is an unreacted monomer when partially polymerized, and an alcohol having an alkyl group having 1 to 20 carbon atoms, as a main constituent unit Monomer (c) containing acrylic ester as a main component; in addition to a mixture of 20 to 90 parts by weight, (meth) acrylic acid and an alkyl having 1 to 4 carbon atoms (Meth) acrylic acid alkyl ester with alcohol having a kill group, ester of (meth) acrylic acid and alicyclic alcohol having 3 to 14 carbon atoms, (meth) acrylic acid and aromatic alcohol having 6 to 14 carbon atoms A monomer having a polymerizable unsaturated bond containing 50% by weight or more of the ester and a conversion rate of 100% without using a reaction solvent is 20000 or less, and a glass transition temperature is 40. ~ 180 ° C tackifying resin (b); an acrylic pressure-sensitive adhesive composition containing 5 to 40 parts by weight and mixed, and containing no solvent (however, component (a) and (The sum of component (b) and component (c) is 100 parts by weight).
  2.   The acrylic pressure-sensitive adhesive composition according to claim 1, wherein the (b) tackifying resin has a weight average molecular weight of 10,000 or less.
  3.   3. The acrylic pressure-sensitive adhesive composition according to claim 2, wherein the tackifying resin (b) has a weight average molecular weight in the range of 400 to 10,000.
  4.   The acrylic pressure-sensitive adhesive composition according to any one of claims 1 to 3, wherein the tackifying resin (b) has a functional group reactive with an epoxy group or an isocyanate group. object.
  5.   The viscosity at 25 ° C of the mixture of the monomer mainly composed of (a) the adhesive polymer and (c) (meth) acrylic acid ester is in the range of 1000 to 100000 cps. The acrylic pressure-sensitive adhesive composition described.
  6.   2. The acrylic pressure-sensitive adhesive composition according to claim 1, wherein the (b) tackifying resin is soluble in a monomer mainly composed of (c) (meth) acrylic acid ester.
  7.   2. The acrylic pressure-sensitive adhesive composition according to claim 1, wherein the acrylic pressure-sensitive adhesive composition further contains, as a crosslinking agent, a compound having an epoxy group and a compound having an isocyanate group.
  8.   A monomer containing 50% by weight or more of (meth) acrylic acid alkyl ester of (meth) acrylic acid and an alcohol having an alkyl group having 1 to 20 carbon atoms as a main constituent unit is partially polymerized by bulk polymerization not containing a solvent. The tacky polymer (a) having a weight average molecular weight of 50,000 or more and a glass transition temperature of 0 to −85 ° C .; 5 to 75 parts by weight of the monomer and the above monomer by bulk polymerization without containing a solvent. (Meth) containing 50% by weight or more of (meth) acrylic acid alkyl ester of (meth) acrylic acid, which is an unreacted monomer when partially polymerized, and an alcohol having an alkyl group having 1 to 20 carbon atoms, as a main constituent unit Monomer (c) containing acrylic ester as a main component; in addition to a mixture of 20 to 90 parts by weight, (meth) acrylic acid and an alkyl having 1 to 4 carbon atoms (Meth) acrylic acid alkyl ester with alcohol having a kill group, ester of (meth) acrylic acid and alicyclic alcohol having 3 to 14 carbon atoms, (meth) acrylic acid and aromatic alcohol having 6 to 14 carbon atoms A monomer having a polymerizable unsaturated bond containing 50% by weight or more of the ester and a conversion rate of 100% without using a reaction solvent is 20000 or less, and a glass transition temperature is 40. -180 ° C. tackifying resin (b); an acrylic pressure-sensitive adhesive composition containing no solvent and containing 5 to 40 parts by weight (provided that (a) component and (b) component) The total amount of the component (c) is 100 parts by weight) and 0.1 to 3 parts by weight of a polymerization initiator with respect to 100 parts by weight of the acrylic pressure-sensitive adhesive composition. Paint with a thickness of 0.01-1.0mm After, method of producing a pressure-sensitive adhesive tape, characterized in that the polymerization.
  9.   The method for producing a pressure-sensitive adhesive tape according to claim 8, wherein the polymerization initiator is a photopolymerization initiator.
  10.   9. The method for producing an adhesive tape according to claim 8, wherein the applied mixture is polymerized by irradiating with ultraviolet rays.
  11.   The weight average molecular weight of said (b) tackifying resin is 10,000 or less, The manufacturing method of the adhesive tape of Claim 8 characterized by the above-mentioned.
  12.   The method for producing a pressure-sensitive adhesive tape according to claim 11, wherein the weight average molecular weight of the (b) tackifying resin is in the range of 400 to 10,000.
  13.   The method for producing a pressure-sensitive adhesive tape according to any one of claims 8 to 11, wherein the tackifying resin (b) has a functional group reactive with an epoxy group or an isocyanate group. .
  14.   9. The viscosity at 25 ° C. of the mixture of the monomer mainly comprising (a) the adhesive polymer and (c) (meth) acrylic acid ester is in the range of 1000 to 100000 cps. The manufacturing method of the adhesive tape of description.
  15.   9. The method for producing a pressure-sensitive adhesive tape according to claim 8, wherein the (b) tackifying resin is soluble in a monomer mainly composed of (c) (meth) acrylic acid ester.
  16.   The said acrylic adhesive composition contains the compound which has a compound which has an epoxy group, and an isocyanate group further as a crosslinking agent, The manufacturing method of the adhesive tape of Claim 8 characterized by the above-mentioned.
  17.   A monomer containing 50% by weight or more of (meth) acrylic acid alkyl ester of (meth) acrylic acid and an alcohol having an alkyl group having 1 to 20 carbon atoms as a main constituent unit is partially polymerized by bulk polymerization not containing a solvent. The tacky polymer (a) having a weight average molecular weight of 50,000 or more and a glass transition temperature of 0 to −85 ° C .; 5 to 75 parts by weight of the monomer and the above monomer by bulk polymerization without containing a solvent. (Meth) containing 50% by weight or more of (meth) acrylic acid alkyl ester of (meth) acrylic acid, which is an unreacted monomer when partially polymerized, and an alcohol having an alkyl group having 1 to 20 carbon atoms, as a main constituent unit Monomer (c) containing acrylic ester as a main component; in addition to a mixture of 20 to 90 parts by weight, (meth) acrylic acid and an alkyl having 1 to 4 carbon atoms (Meth) acrylic acid alkyl ester with alcohol having a kill group, ester of (meth) acrylic acid and alicyclic alcohol having 3 to 14 carbon atoms, (meth) acrylic acid and aromatic alcohol having 6 to 14 carbon atoms A monomer having a polymerizable unsaturated bond containing 50% by weight or more of the ester and a conversion rate of 100% without using a reaction solvent and a weight average molecular weight of 20000 or less, and a glass transition temperature of 40 ~ 180 ° C tackifying resin (b); an acrylic pressure-sensitive adhesive composition containing no solvent and containing 5 to 40 parts by weight (mixed (a) component and (b) component) The total amount of the component (c) is 100 parts by weight) and 0.1 to 3 parts by weight of a polymerization initiator with respect to 100 parts by weight of the acrylic pressure-sensitive adhesive composition. Application with thickness of 0.01-1.0mm After the adhesive tape, characterized in that obtainable by polymerizing.
  18.   18. The pressure-sensitive adhesive tape according to claim 17, wherein a monomer containing (c) (meth) acrylic acid ester as a main component does not remain in the pressure-sensitive adhesive tape.
  19.   18. The pressure-sensitive adhesive tape according to claim 17, wherein the pressure-sensitive adhesive tape has a crosslinked structure formed of an epoxy-based compound and / or a crosslinked structure formed of an isocyanate-based compound.
  20.   The pressure-sensitive adhesive tape according to claim 17, wherein the acrylic pressure-sensitive adhesive composition further contains a compound having an epoxy group and a compound having an isocyanate group as a crosslinking agent.
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